JPH0449560B2 - - Google Patents

Info

Publication number: JPH0449560B2
Authority: JP; Japan
Prior art keywords: complex; trans; platinum; cis; diaminocyclohexane
Prior art date: 1984-03-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP60040975A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6133192A (ja

Inventor

Eru Narayanan Ben

Kee Uorupaatoodefuitsupusu Merii

Deii Hooguitsutsu Rudeigaa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

US Department of Energy

United States Department of Commerce

Original Assignee

US Department of Energy

United States Department of Commerce

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-03-01

Filing date

1985-03-01

Publication date

1992-08-11

1985-03-01 Application filed by US Department of Energy, United States Department of Commerce filed Critical US Department of Energy

1986-02-17 Publication of JPS6133192A publication Critical patent/JPS6133192A/ja

1992-08-11 Publication of JPH0449560B2 publication Critical patent/JPH0449560B2/ja

Status Granted legal-status Critical Current

Links

SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims abstract description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 106
229910052697 platinum Inorganic materials 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 18
206010028980 Neoplasm Diseases 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 15
201000011510 cancer Diseases 0.000 claims description 8
230000001093 anti-cancer Effects 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
229940121363 anti-inflammatory agent Drugs 0.000 claims 1
239000002260 anti-inflammatory agent Substances 0.000 claims 1
230000000118 anti-neoplastic effect Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
150000001875 compounds Chemical class 0.000 description 39
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 24
229960004316 cisplatin Drugs 0.000 description 23
241001465754 Metazoa Species 0.000 description 18
238000011282 treatment Methods 0.000 description 17
230000000694 effects Effects 0.000 description 16
238000000034 method Methods 0.000 description 16
238000002474 experimental method Methods 0.000 description 15
230000004083 survival effect Effects 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
229940079593 drug Drugs 0.000 description 12
239000003814 drug Substances 0.000 description 12
238000002347 injection Methods 0.000 description 11
239000007924 injection Substances 0.000 description 11
150000003057 platinum Chemical class 0.000 description 11
239000007787 solid Substances 0.000 description 11
239000000126 substance Substances 0.000 description 9
239000002246 antineoplastic agent Substances 0.000 description 8
230000004071 biological effect Effects 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
238000011160 research Methods 0.000 description 7
SSJXIUAHEKJCMH-OLQVQODUSA-N (1s,2r)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-OLQVQODUSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000037396 body weight Effects 0.000 description 6
239000000047 product Substances 0.000 description 6
241000894007 species Species 0.000 description 6
230000000259 anti-tumor effect Effects 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000004985 diamines Chemical class 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
210000004881 tumor cell Anatomy 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000008859 change Effects 0.000 description 4
238000011161 development Methods 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
230000007774 longterm Effects 0.000 description 4
230000009467 reduction Effects 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
230000000719 anti-leukaemic effect Effects 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
208000032839 leukemia Diseases 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
NNWOGVOYLDMOAZ-UHFFFAOYSA-L (2-azanidylcyclohexyl)azanide;benzene-1,2,4-tricarboxylate;hydron;platinum(4+) Chemical compound [H+].[Pt+4].[NH-]C1CCCCC1[NH-].[O-]C(=O)C1=CC=C(C([O-])=O)C(C([O-])=O)=C1 NNWOGVOYLDMOAZ-UHFFFAOYSA-L 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
229940041181 antineoplastic drug Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
102000005936 beta-Galactosidase Human genes 0.000 description 2
108010005774 beta-Galactosidase Proteins 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
230000006698 induction Effects 0.000 description 2
238000011221 initial treatment Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
231100001231 less toxic Toxicity 0.000 description 2
-1 of the Pt () family Chemical compound 0.000 description 2
239000003921 oil Substances 0.000 description 2
CCKKXHSVRWBMKY-UHFFFAOYSA-N platinum;1,2,3,3-tetrachlorocyclohexane-1,2-diamine Chemical compound [Pt].NC1(Cl)CCCC(Cl)(Cl)C1(N)Cl CCKKXHSVRWBMKY-UHFFFAOYSA-N 0.000 description 2
230000004044 response Effects 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 1
POQBJIOLWPDPJE-KGZKBUQUSA-N (1r,2r)-cyclohexane-1,2-diamine;platinum Chemical compound [Pt].N[C@@H]1CCCC[C@H]1N POQBJIOLWPDPJE-KGZKBUQUSA-N 0.000 description 1
UUERTZXRKZEANK-UHFFFAOYSA-L (2-azanidylcyclohexyl)azanide;dichloroplatinum(2+) Chemical compound C1CCCC2N[Pt](Cl)(Cl)NC21 UUERTZXRKZEANK-UHFFFAOYSA-L 0.000 description 1
KVFQUEDZECDHKS-UHFFFAOYSA-J (2-azanidylcyclohexyl)azanide;tetrachloroplatinum(2+) Chemical compound Cl[Pt+2](Cl)(Cl)Cl.[NH-]C1CCCCC1[NH-] KVFQUEDZECDHKS-UHFFFAOYSA-J 0.000 description 1
KUWPCJHYPSUOFW-SCWFEDMQSA-N (2r,3r,4s,5r)-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)OC1OC1=CC=CC=C1[N+]([O-])=O KUWPCJHYPSUOFW-SCWFEDMQSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
DDRVFRXYTKAZHH-UHFFFAOYSA-N 2-carboxyoxycarbonylbenzoic acid Chemical compound OC(=O)OC(=O)C1=CC=CC=C1C(O)=O DDRVFRXYTKAZHH-UHFFFAOYSA-N 0.000 description 1
KUWPCJHYPSUOFW-YBXAARCKSA-N 2-nitrophenyl beta-D-galactoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1[N+]([O-])=O KUWPCJHYPSUOFW-YBXAARCKSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000031648 Body Weight Changes Diseases 0.000 description 1
OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
230000008265 DNA repair mechanism Effects 0.000 description 1
206010059866 Drug resistance Diseases 0.000 description 1
206010014418 Electrolyte imbalance Diseases 0.000 description 1
241000701959 Escherichia virus Lambda Species 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
208000007093 Leukemia L1210 Diseases 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
206010034133 Pathogen resistance Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
238000001237 Raman spectrum Methods 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
230000007815 allergy Effects 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
230000004579 body weight change Effects 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
210000000349 chromosome Anatomy 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000009838 combustion analysis Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
ZYZCZCHRQQZTHI-UHFFFAOYSA-N cyclohexane-1,1-diamine;platinum Chemical compound [Pt].NC1(N)CCCCC1 ZYZCZCHRQQZTHI-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000009509 drug development Methods 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000002513 implantation Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000005917 in vivo anti-tumor Effects 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000008693 nausea Effects 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
210000000578 peripheral nerve Anatomy 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
BASFCYQUMIYNBI-IGMARMGPSA-N platinum-195 Chemical compound [195Pt] BASFCYQUMIYNBI-IGMARMGPSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000002381 testicular Effects 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
238000011277 treatment modality Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

JP4097585A 1984-03-01 1985-03-01 異性体的に純粋なテトラハロ（１，２−ジアミノシクロヘキサン）プラチナ（４）錯体およびその用途 Granted JPS6133192A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/585,111 US4599352A (en)	1984-03-01	1984-03-01	Antineoplastic platinum (IV) complexes and compositions
US585111		1984-03-01

Publications (2)

Publication Number	Publication Date
JPS6133192A JPS6133192A (ja)	1986-02-17
JPH0449560B2 true JPH0449560B2 (de)	1992-08-11

Family

ID=24340085

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4097585A Granted JPS6133192A (ja)	1984-03-01	1985-03-01	異性体的に純粋なテトラハロ（１，２−ジアミノシクロヘキサン）プラチナ（４）錯体およびその用途

Country Status (10)

Country	Link
US (1)	US4599352A (de)
EP (1)	EP0154589B1 (de)
JP (1)	JPS6133192A (de)
AT (1)	ATE45361T1 (de)
AU (1)	AU575913B2 (de)
CA (1)	CA1251457A (de)
DE (1)	DE3572175D1 (de)
DK (1)	DK97085A (de)
IL (2)	IL74449A (de)
IT (1)	IT1200393B (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL74449A (en) *	1984-03-01	1988-07-31	Us Commerce	Tetrahalo-1,2-cyclohexane-diamino platinum complexes and anti-neoplastic compositions comprising them
US4658047A (en) *	1985-09-27	1987-04-14	The United States Of America As Represented By The Department Of Health And Human Services	Method of preparing 1,2-diaminocyclohexane tetrachloro platinum (IV) isomers
JPS62207283A (ja) *	1986-03-07	1987-09-11	Yoshinori Kitani	新規な白金錯体
US5011959A (en) *	1986-11-17	1991-04-30	The Board Of Regents, The University Of Texas System	1,2-diaminocyclohexane-platinum complexes with antitumor activity
GB8806224D0 (en) *	1988-03-16	1988-04-13	Johnson Matthey Plc	Platinum chemotherapeutic product
US5393909A (en) *	1988-11-22	1995-02-28	Board Of Regents, The University Of Texas System	Diamine platinum complexes as antitumor agents
JPH06287021A (ja) *	1992-04-22	1994-10-11	Tanaka Kikinzoku Kogyo Kk	光学活性な白金錯化合物の光学的分割方法
JP3025602B2 (ja) *	1993-05-21	2000-03-27	デビオファームエス．アー．	光学的に高純度なシス−オキザラート（トランス−ｌ−１，２−シクロヘキサンジアミン）白金（ＩＩ）錯体の製造方法
US5648384A (en) *	1993-10-04	1997-07-15	Tanaka Kikinzoku Kogyo K.K.	Anti-tumor platinum (IV) complex
JP3154399B2 (ja) *	1996-07-04	2001-04-09	デビオファームエス．アー．	白金化合物の製造方法
US5659868A (en) *	1995-12-11	1997-08-19	Xerox Corporation	Pressure roll having a flat shaft for use in a heat and pressure fuser apparatus
WO2000006134A2 (en) *	1998-07-30	2000-02-10	Sigma-Tau Industrie Farmaceutiche Riunite S.P.A.	Use of l-carnitine and its alkanoyl derivatives in the preparation of medicaments with anticancer activity
US20030199535A1 (en) *	1998-07-30	2003-10-23	Claudio Cavazza	Method for preventing and/or treating peripheral neuropathies induced by the administration of an anticancer agent
CZ294382B6 (cs) *	1999-09-29	2004-12-15	Pliva-Lachema A.S.	Způsob přípravy cis-dichloro-(trans-l-1,2-cyklohexandiamin)platnatého komplexu
HK1049787B (en)	1999-10-01	2014-07-25	Immunogen, Inc.	Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
WO2011031839A2 (en) *	2009-09-10	2011-03-17	International Maritime Security Corporation	Watercraft, water diverter, entanglement system, and defense system for watercraft
US10183027B2 (en) *	2016-09-21	2019-01-22	Hong Kong Baptist University	Lanthanide toolbox for multi-modal, non-invasive tumor specific theranostic prodrugs

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4177263A (en) *	1972-02-28	1979-12-04	Research Corporation	Anti-animal tumor method
JPS5829957B2 (ja) *	1977-09-12	1983-06-25	喜徳喜谷	新規な白金錯体
US4329299A (en) *	1979-08-23	1982-05-11	Johnson, Matthey & Co., Limited	Composition of matter containing platinum
NL181434C (nl) *	1980-01-03	1987-08-17	Tno	Platina(iv)-diamine-complexen, alsmede hun bereiding en toepassing.
NL8101026A (nl) *	1981-03-03	1982-10-01	Tno	Platinadiamine-complexen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een dergelijk platinadiamine-complex voor de behandeling van kanker alsmede aldus verkregen gevormd geneesmiddel.
AU3409884A (en) *	1983-10-19	1985-04-26	Nippon Kayaku Kabushiki Kaisha	Platinum complexes
GB8328218D0 (en) *	1983-10-21	1983-11-23	Johnson Matthey Plc	Oral compositions
IL74449A (en) *	1984-03-01	1988-07-31	Us Commerce	Tetrahalo-1,2-cyclohexane-diamino platinum complexes and anti-neoplastic compositions comprising them

1984
- 1984-03-01 IL IL74449A patent/IL74449A/xx not_active IP Right Cessation
- 1984-03-01 US US06/585,111 patent/US4599352A/en not_active Expired - Lifetime
1985
- 1985-02-27 IL IL74449A patent/IL74449A0/xx unknown
- 1985-02-27 EP EP85400372A patent/EP0154589B1/de not_active Expired
- 1985-02-27 DE DE8585400372T patent/DE3572175D1/de not_active Expired
- 1985-02-27 AT AT85400372T patent/ATE45361T1/de not_active IP Right Cessation
- 1985-02-28 AU AU39269/85A patent/AU575913B2/en not_active Ceased
- 1985-03-01 DK DK97085A patent/DK97085A/da not_active Application Discontinuation
- 1985-03-01 JP JP4097585A patent/JPS6133192A/ja active Granted
- 1985-03-01 IT IT8519727A patent/IT1200393B/it active
- 1985-03-01 CA CA000475564A patent/CA1251457A/en not_active Expired

Also Published As

Publication number	Publication date
US4599352A (en)	1986-07-08
IL74449A0 (en)	1985-05-31
EP0154589A2 (de)	1985-09-11
DK97085D0 (da)	1985-03-01
JPS6133192A (ja)	1986-02-17
EP0154589A3 (en)	1986-01-15
DE3572175D1 (en)	1989-09-14
IT8519727A0 (it)	1985-03-01
IL74449A (en)	1988-07-31
EP0154589B1 (de)	1989-08-09
CA1251457A (en)	1989-03-21
AU3926985A (en)	1985-09-05
ATE45361T1 (de)	1989-08-15
IT1200393B (it)	1989-01-18
DK97085A (da)	1985-09-02
AU575913B2 (en)	1988-08-11

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